


Impassioned Plea

by DRHPaints



Category: Conan O’Brien, Conan O’Brien RPF, Late Night Host RPF
Genre: Blow Jobs, Conan O’Brien - Freeform, Conan O’Brien Needs A Friend Podcast, Cunnilingus, Explicit Language, Explicit Sexual Content, F/M, Face-Fucking, One Shot, Orgasm Delay/Denial, Restraints, Vaginal Fingering
Language: English
Status: Completed
Published: 2020-08-02
Updated: 2020-08-02
Packaged: 2021-03-05 19:20:25
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,355
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25660504
Author URL: https://archiveofourown.org/users/DRHPaints/pseuds/DRHPaints
Summary: Gwendolyn Greene is a renowned author who’s been invited to the ‘Conan O’Brien Needs a Friend’ podcast. When things heat up between her and Conan, he invites her back to his place for a good time.
Relationships: Conan O’Brien/Original Female Character
Comments: 2
Kudos: 7





	Impassioned Plea

**Author's Note:**

> Thank you for reading! If you enjoy this please leave a comment or come say hi on Tumblr at fandomtransmandom :-)

Looking in the mirror, Gwendolyn touched up her eyeliner before fluffing out her hair and checking her teeth. She’d been on his show a couple of times, but being invited to the podcast was something else entirely. Compared to the rushed experience of a brief encounter backstage, ten minutes of light chat in front of a studio audience, and hurried comments made during commercial breaks, the idea of sitting across from Conan for nearly an hour in close quarters was exhilarating.  
Gwendolyn smoothed her hands over her purple knee-length summer dress and put on a mustard yellow cardigan, climbed in the car and made her way to the recording studio. On the way she thought back to her last time on the show. Conan came off just a little bit flirtatious. _Maybe he’s just like that_ , she thought. Perhaps it was a natural by-product of his charisma, a necessary aspect of Conan's career as a talk show host. The winning smile, the way Conan's tall form would angle itself ever so gently into her space, how his fingers ghosted over her arm…  
Shaking her head, Gwendolyn forced herself to focus on the road, and soon she arrived, parking and checking her appearance one last time in the rear view mirror. When Gwendolyn entered the building she approached a security desk and was directed to the elevator. Reaching the desired floor, she stood before the room and Sona opened the door, smiling.  
“Hi Gwen, come on in.” Sona stepped back, and Gwendolyn entered, looking around. She saw producer Matt Gourley sitting in front of a computer and a plethora of equipment she couldn’t begin to name, and of course, Conan. Standing to greet her, he wore black skinny jeans and a matching polo, hair unkempt in a way she’d never seen before. _He looks freshly fucked_. The thought occurred to Gwendolyn before she could stop it and she felt the hair on the back of her neck rise. Conan was also sporting glasses with thick black frames, which were especially endearing.  
“Gwen, hey! Good to see you!” Conan extended his arms for a hug, and as she embraced him she noticed again how good he smelled, though she was never quite able to place the scent.   
“Hey Conan, thanks for having me, excited to be here.” Gwendolyn nodded and Conan gestured to a chair. Sitting down, Conan joined her, putting a pair of headphones on.  
“Well, it’s pretty self explanatory.” Conan touched his index finger to the corner of his lip. “We’ll just chat for about forty-five minutes or so, nothing all that structured, see how things go. Sound good?”  
Gwendolyn nodded. “Yeah, great.”  
“Oh, and one more thing,” Matt Gourley piped up. “The first thing we need to record is your fill-in-the-blank. You know, ‘I feel ____ about being Conan O’Brien’s friend’.”  
“Oh right, of course,” Gwendolyn nodded, putting on her headphones. Watching as Gourley tapped away, he eventually pointed at her and she took a deep breath. _Fuck it._  
“Hello, my name is Gwendolyn Greene, and I feel _impassioned_ about being Conan O’Brien’s friend.” Locking onto Conan’s crystalline blue eyes as she said it, Gwendolyn saw his Adam’s apple bob up and down as he blinked.   
“Well, um…” Conan cleared his throat, adjusting his glasses. “We’re sitting here with Gwendolyn Greene, best-selling author, _Hugo Award_ winner, and always a joy to have on the show. How are you doing today, Gwen?”  
“I’m doing well, Conan. Thank you for having me.” Gwendolyn smiled. “How are you doing?”  
Conan nodded. “I’m doing well, thanks for asking. Now,” He referenced his notes. “You’ve written three books in the _Dragon’s Hide_ series and the fourth is due out in October, people love these things, myself included. What has it been like for you since the series hit it big?”  
Gwendolyn leaned in towards the microphone, and she thought she saw Conan’s eyes drift down to peek at her cleavage, but when she looked again he was grinning expectantly at her face. “Well, it’s been wild. What with people dressing up at conventions, and even some folks who name their babies after characters, I never could’ve predicted anything like that. But of course, not everyone’s a fan.” Gwendolyn chuckled.  
“Right.” Conan licked his thin lips. “Over the years there have been some conservative groups that have, shall we say, taken issue with certain aspects of your writing, is that fair to say?”  
Laughing, Gwendolyn nodded. “That’s a diplomatic way of putting it. Basically there are a lot of uptight people out there who think I’m a tramp for putting so much sex in my books.”  
Holding his belly, Conan threw back his head and laughed, face scrunched tight, and Gwendolyn couldn’t help but titter herself. “Well, personally I’m very grateful.” Conan leaned into the microphone. “I find your writing incredibly erotic.” He lowered his voice and raised an eyebrow, and though he was probably trying to be funny, Gwendolyn began to tingle.  
“Why, thank you.” She lifted a hand to her cheek. “I do my best.”  
They spent the rest of the podcast discussing books, comedy, and their lives. When they wrapped, Gwendolyn removed her headphones, thanking Gourley and saying goodbye to Sona. Conan kindly offered to walk her to the car, and as he pushed the lobby button in the elevator Gwendolyn once again noticed the scent of his cologne in the air.  
“That was really fun, thanks again for having me.” Gwendolyn smiled up at his tall frame.  
Conan nodded, wiggling his orange hair. “Of course, I’m glad you were fr—“  
With a metallic grinding sound and a shudder, lights flickering once, the elevator came to a halt. Holding their hands out to steady themselves, Conan and Gwendolyn looked at each other.  
“Okay, that’s not good…” Conan muttered, glancing at the ceiling. Stepping forward, he pushed the alarm button. After about a minute and a crackle of static, a man’s voice came through.  
“Maintenance, what seems to be the problem?” Conan gave the address and explained they were stuck. “Okay, well both my crews are out on jobs right now, so it might be a bit of a wait. Hold tight and we’ll get you out as soon as possible.” The voice abruptly cut out and Conan sighed.  
“Well, guess there’s not much we can do.” Conan leaned against the back wall.  
Perking her ears up, Gwendolyn noticed Kate Bush’s _Running Up That Hill_ wafting overhead. “At least the music is good.” She shrugged. “And the company.”  
Conan raised a pale orange eyebrow. “Aw, come on.You’re too young to know this song.”  
Gwendolyn scoffed in mock defiance. “I beg your pardon, sir? I take umbrage to that comment.”  
Smirking, Conan crossed his arms. “Oh really? Umbrage?”  
“Yes.” Gwendolyn bit her lip, raising an eyebrow. “Severe umbrage. I love 80’s music.”  
Nodding, Conan looked to the ceiling. “It is a great song.”  
Gwendolyn looked to the floor, shifting her weight. “Would you want to…dance? To pass the time?” Flicking her eyes up to him, she saw Conan blink rapidly.  
“Dance?” He cleared his throat.  
Nodding, she took half a step, lifting her face towards his so they were only inches apart. “Yeah…”  
Conan stared down at her for a moment, energy crackling between them as he clenched his jaw. “O-okay then.”  
Smiling, Gwendolyn wound her arms around his neck, Conan’s hands finding their way to her waist. Gently swaying, Gwendolyn brought herself closer after a few steps, emerald eyes never breaking from Conan’s, grateful when the circle of his arms tightened and sank to her hips. Gwendolyn could feel the rise and fall of his chest now, its gradual increase in speed, and as she brought her face near to his she studied the elegant outline of Conan's slender lips. Mouths finally meeting, Gwendolyn's eyes dropped closed as she felt the buzz of Conan’s pleased humming against her lips, his tongue sneaking in to dance with her own, heads tipping to the side as she wound her hand into that tantalizing hair she ached to touch.  
Suddenly it was as if someone touched a match to a fuse. Mouths frantically attempting to swallow one another, hands groping in a frenzy, they tore at each other savagely, Gwendolyn’s cardigan bunched on the floor as she jumped and wrapped her legs around Conan’s waist, who slammed her against the wall of the elevator.  
Frantically he snatched down the front of her dress along with her bra, grabbing at her breasts while their mouths mashed against one another. Fiddling with the button and fly of his jeans, Gwendolyn found herself breathing hard into his mouth as a large freckled hand slid into her panties and began teasing at her wet arousal. Gwendolyn just managed to get her hand below the waistband of his boxers, gripping his long, stiff cock when—  
_WHOOSH! CLANG_! The elevator shuddered back to life, descending towards the ground floor. Looking at each other wide eyed, Conan let her down and they hurriedly put themselves back together, Conan willing his erection to go away while Gwendolyn desperately tried to smooth out her hair and replace her cardigan. Glancing at each other before the ding, they gave a subtle nod, and when the door opened it revealed a tubby maintenance man in blue overalls, along with Matt and Sona standing there, the last two looking concerned.  
“Oh my goodness, are you guys okay?” Sona asked, running a hand through her mass of thick brown hair.  
Conan nodded, trying to angle his body effectively. He managed to get his erection to go down for the most part, but anyone looking closely would be able to tell. “Yeah, we’re fine.” Gwendolyn nodded in agreement.  
“Are you sure?” Sona looked back and forth between them. “You look pretty shaken up…”   
Shrugging, Gwendolyn said, “I just don’t care for confined spaces much, I guess.”  
Forcing a smile, Conan nodded in agreement. “Well, I’ll walk you to your car.”   
Once they were outside, Gwendolyn leaned in to him with a low voice. “How much longer are you going to be here?” Looking up at him through her eyelashes, Conan felt his cock throb again and he bit the inside of his lip.  
“An hour or two, maybe.” Conan ran a single finger down her forearm. “Do you want to come to my place later?”  
“Yes.” Gwendolyn answered immediately. Maybe it made her sound too eager, but she didn’t care.   
Smiling, Conan fished into his pocket and they exchanged numbers. Texting her his address, Conan promised to let her know when they were wrapping up before peering around and leaning in for a quick kiss. Gwendolyn grabbed the sides of his polo collar and held him, finally parting and letting her hands trail down his chest before getting in her car and heading home.

  
**

Adjusting her breasts in the tiny black dress, Gwendolyn examined herself in the mirror. The dress was so short she never dared to wear it out in public, since she couldn’t really bend over in it. But she figured it was highly unlikely they’d be going out. _Hell, I probably won’t be wearing it long anyway_ …  
She was applying a blood red lipstick when her phone buzzed on the counter.

_I’ll be home in 20 minutes or so. Meet you there?_

Grinning, Gwendolyn responded in the affirmative, finishing her makeup and heading out. When she pulled up to Conan’s house, she parked behind his Tesla and walked up to the door, pressing the bell.   
Conan appeared, still wearing the black skinny jeans, but he’d swapped out the polo for a flattering dark green Henley. “Uh..wow.” He looked her up and down. “You look amazing." Conan stepped aside and she walked in.  
“Thank you.” Heels clicking on the hardwood floor, she peered around the spacious house, tastefully appointed but not pretentious.   
“Would you like something to drink? A glass of wine?” Conan suggested.  
Gwendolyn shrugged. “Sure, if you’re having one."  
Nodding, Conan grabbed two glasses from the cabinet and poured a Pinot Noir. Gwendolyn took a sip, staring at him over the rim of her drink. They drank silently for a minute, eyes locked, before Conan intently set his glass down, walked around the kitchen island and took Gwendolyn’s from her hand, grabbing her fiercely by the waist and dragging her to him, one hand bunched in her auburn waves, the other clutching her round ass while he fused their mouths together. Lifting her leg to wrap around him, Conan pressed her against the counter for a moment before breaking away.  
“Bedroom?” He asked, pale skin flushed pink.  
Gwendolyn nodded enthusiastically and followed him. Once inside, Conan’s arms encircled her, and as they kissed he reached for the hem of her dress, pulling it overhead and casting it aside to reveal her black lace bra and panties. Cupping her breast, he massaged her gently while Gwendolyn peeled off his Henley.   
“Hey,” Conan stepped back, circling her cheekbone with his thumb. “Are you up for something…adventurous?”  
Gwendolyn narrowed her eyes at him. “How do you mean?”  
“Well,” Conan leaned into her, brushing his lips over the spot where her jaw joined her neck. “Maybe I could…” He trailed the backs of his fingers over one of her breasts, down her abdomen, landing to tickle between her legs.“ _Tie_ _you up_.”  
Shivering, Gwendolyn’s fingertips curled into his shoulders and her knees buckled slightly. “Yes." She breathed. Conan grinned, hooking a finger under her chin and kissing her again, all the while delicately petting her through the fabric of her panties, pleased as they grew damp beneath his touch.  
Guiding her by the waist, Conan directed Gwendolyn to lay back on the large bed, reaching underneath for a box and extracting four strips of silk fabric. Setting them down for a moment, Conan unbuckled his jeans, sliding them to the floor along with his boxers, crawling into the bed after her.   
As he laid his naked weight on top of her, Gwendolyn let out a delighted sigh, reaching behind herself to undo her bra and tossing it to the floor. Conan lowered his hips against her, the column of his erection grinding between Gwendolyn's legs, the only thing separating them a thin layer of lace. Rolling together, Conan waited until Gwendolyn was anxiously lifting her hips to his every stroke before stopping and sitting back on his heels. Removing her panties, he got off the bed, and picking up the silk strips he went from post to post, starting with her ankles, and began to tie her spread-eagled to the bed.  
Gwendolyn watched him as he restrained her. Cerulean eyes blazing with lust, large freckled hands tugging the knots forcefully, stiff cock insistently curving below his navel. Finishing with her right wrist, Conan hopped back on the bed, settling on his knees between her legs and began to achingly explore. First, he used two fingers to make tiny circles around her clit, eventually replacing them with his tongue and tightening his movements, but never quite hitting home.   
Drawing his body close to hers, Conan lifted her ass slightly and positioned his cock at her entrance, and she prepared for him to slide inside. Instead, however, he began rubbing the head of his cock up and down her slit, slick with her desire, and every time he grazed her swollen clit a helpless mewl escaped Gwendolyn's lips. Sometimes Conan would place the tip right up against her clit and wiggle. _Hard_. Straining against her bonds, Gwendolyn thrashed about, unsure how much longer she could tolerate this treatment.  
“ _Fuck, Conan, please."_ Gwendolynbegged, eyes closed, head digging into the mattress.  
“Please what?” Conan’s voice was deep and dangerous as he continued dragging his cock over her.  
“ _Please, please, just let me cum, fuck, please._ ” Gwendolyn whined, tossing her head from side to side.   
Conan slid just the tip of his cock inside of her. “Is this what you want?”  
“ _Yes, please, fuck me, yes_!” She cried, tugging against the ties around her ankles in a desperate attempt to drive him deeper inside herself, but before she had even half a chance Conan whipped his cock away.  
“What about this?” Conan lowered his mouth, and making his tongue wide and flat, he licked up her opening with agonizing leisure, sucking ever so lightly when he reached her clit for only a second, causing Gwendolyn to cry out and retract her whole body as much as she was able given her condition.  
“ _Please, Conan, PLEASE_!” Gwendolyn knew it sounded undignified, but she was beyond caring. Conan tiptoed his fingers up her legs, over her abdomen, caressing her breasts, kissing and nibbling her neck as he touched her arms, held her face, large freckled hands and thin lips gracing every inch of her they could reach, except the one she wanted.  
Without warning, Conan sheathed the entirety of his thick cock deep inside her, fingering her clit furiously with one hand and burying the other in her auburn hair. Gwendolyn’s mouth fell open in a silent scream, eyes rolling back in her head, body erupting in a violent earthquake of tremors that made her appear possessed underneath him as Conan pounded into her. And then suddenly, Gwendolyn went slack against the bonds, eyes falling closed and head tipping to the side.   
Conan sighed, reaching up to feel her pulse. Strong and normal. Grinning to himself, Conan got out of bed and went to the kitchen. It wasn’t the first time this happened to him. Conan retrieved two ice cubes from the freezer, persistent erection almost painful as he padded back to the bedroom.   
Holding one ice cube to the back of Gwendolyn’s neck, Conan placed the other on her forehead. “ _GWEN_!” He shouted near her face, applying pressure to the ice.  
Awaking with a snort, Gwendolyn looked around disoriented, and Conan quickly jogged to the bathroom to toss the ice cubes in the sink, returning to kneel at the bedside, delicately stroking Gwendolyn’s face. “You alright?” He smiled up at her.  
“What happened?” She blinked, peering around the room.  
Conan tried to stay humble and swallow the smirk that came to his lips, but he was struggling. “Well, you…you came so hard you passed out.”  
She raised her eyebrows, frowning appraisingly. “Wow…well." She nodded. “Good job, then.” Conan chuckled and shook his head. Gwendolyn looked down between his legs, seeing his engorged, purple cock. “You want me to do something about that?”  
Conan licked his lips. “What did you have in mind?”  
Leaning as far forward as she could, Gwendolyn breathed. “ _Get up here and fuck my face_.”  
Shuddering, Conan’s nose flared and he nodded, climbing on top of her, one knee on either side of her shoulders, careful not to rest too much of his weight back on her chest.  
“Ready?” Conan held the tip of his cock near her lips. Flicking out her tongue to lick the slit, she nodded and Conan leaned forward until he was half-ensconced in her throat, Gwendolyn hollowing her cheeks and shoving her tongue against the underside of his cock. Rocking himself further, Conan put one hand in her hair, the other holding the top of the headboard, lost in the warm sensation of her moist mouth.  
“ _Oh fuck, Gwen, yes. Yes, just like that."_ Conan groaned, thrusting his hips in earnest as Gwendolyn moaned around his sensitive flesh. Burying himself deep in her throat, Conan grew close, body curving, forehead resting against the wall, a high pitched whimper escaping him as he came, shooting hot cum down the back of her throat, straining forward as he cradled her head against his pulsing cock.  
Gradually recovering, Conan withdrew and climbed off, breathing hard. He began to untie the knots at her wrist, proceeding around the bed until Gwendolyn was free and stood to bend and stretch. Catching her about the waist, he leaned his forehead against hers.  
“Well, that was fun." Conan casually drew circles along the small of her back.   
“Mmhmm.” Gwendolyn trailed her fingers over his orange chest hair, grinning. “Next time, it’s your turn.”  
  



End file.
